Pentanoic acid (YMDB01484)

Identification

YMDB ID

YMDB01484

Name

Pentanoic acid

Species

Saccharomyces cerevisiae

Strain

Brewer's yeast

Description

Valeric acid (pentanoic acid) is a straight-chain alkyl carboxylic acid with a very unpleasant odor. It is found naturally in the perennial flowering plant valerian (Valeriana officinalis), from which it gets its name. Volatile esters of valeric acid tend to have pleasant odors and are used in perfumes and cosmetics. Ethyl valerate and pentyl valerate are used as food additives because of their fruity flavors.

Structure

MOL SDF PDB SMILES InChI

Synonyms

1-Butanecarboxylate
1-Butanecarboxylic acid
1-pentanoate
1-pentanoic acid
Butanecarboxylate
Butanecarboxylic acid
CH3-[CH2]3-COOH
Kyselina valerova
n-BuCOOH
n-C4H9COOH
n-Pentanoate
n-Pentanoic acid
n-Valerate
n-valeric acid
Pentanoate
Pentanoic acid
pentoate
pentoic acid
Propylacetate
Propylacetic acid
Valerate
Valerianate
Valerianic acid
Valeriansaeure
Valeriansaure
Valeric acid
Valeric acid normal
Valeric acid, n-
Valeric acid, normal
Valerate, normal
N-Pentanoic acid, ammonium salt
N-Pentanoic acid, potassium salt
N-Pentanoic acid, sodium salt
N-Pentanoic acid, zinc salt
N-Pentanoic acid, maganese (+2) salt
N-Pentanoic acid, 11C-labeled
Lithium pentanoate
N-Pentanoic acid, 11C-labeled sodium salt

CAS number

109-52-4

Weight

Average: 102.1317
Monoisotopic: 102.068079564

InChI Key

NQPDZGIKBAWPEJ-UHFFFAOYSA-N

InChI

InChI=1S/C5H10O2/c1-2-3-4-5(6)7/h2-4H2,1H3,(H,6,7)

IUPAC Name

pentanoic acid

Traditional IUPAC Name

N-valeric acid

Chemical Formula

C₅H₁₀O₂

SMILES

CCCCC(O)=O

Chemical Taxonomy

Description

belongs to the class of organic compounds known as straight chain fatty acids. These are fatty acids with a straight aliphatic chain.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Fatty Acyls

Sub Class

Fatty acids and conjugates

Direct Parent

Straight chain fatty acids

Alternative Parents

Substituents

Straight chain fatty acid
Monocarboxylic acid or derivatives
Carboxylic acid
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

straight-chain saturated fatty acid (CHEBI:17418 )
short-chain fatty acid (CHEBI:17418 )
Straight chain fatty acids (C00803 )
Saturated fatty acids (C00803 )
Straight chain fatty acids (LMFA01010005 )

Physical Properties

State

Liquid

Charge

Melting point

-34 °C

Experimental Properties

Property	Value	Reference
Water Solubility	24 mg/mL at 25 oC [YALKOWSKY,SH & HE,Y (2003)]	PhysProp
LogP	1.39 [HANSCH,C ET AL. (1995)]	PhysProp

Predicted Properties

Property	Value	Source
Water Solubility	40.3 g/L	ALOGPS
logP	1.34	ALOGPS
logP	1.37	ChemAxon
logS	-0.4	ALOGPS
pKa (Strongest Acidic)	5.01	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	37.3 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	26.47 m³·mol⁻¹	ChemAxon
Polarizability	11.23 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Biological Properties

Cellular Locations

Not Available

Organoleptic Properties

Flavour/Odour	Source
Acidic	FDB003230
Animal	FDB003230
Putrid	FDB003230
Rancid	FDB003230
Sickening	FDB003230
Sweat	FDB003230
Sweaty	FDB003230

SMPDB Pathways

Not Available

KEGG Pathways

Not Available

SMPDB Reactions

Not Available

KEGG Reactions

Not Available

Concentrations

Intracellular Concentrations

Not Available

Extracellular Concentrations

Not Available

Spectra

Spectrum Type	Description	Splash Key	View
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-03fr-9000000000-5ef705125c3c70ad3df3	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-03di-9000000000-2160417549a364f722df	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-03fr-9000000000-5ef705125c3c70ad3df3	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-03di-9000000000-2160417549a364f722df	JSpectraViewer \| MoNA
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-004l-9000000000-317b810c8d610eaf0188	JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positive	splash10-05dr-9200000000-cfee4e723931c0c4882e	JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	JSpectraViewer
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)	splash10-0kdi-9200000000-68de4edfab1763d25290	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)	splash10-0006-9000000000-5807dc032b484168ad7f	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)	splash10-0006-9000000000-6815adcb2b82e3f1f29f	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - EI-B (HITACHI RMU-6M) , Positive	splash10-03fr-9000000000-5ef705125c3c70ad3df3	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - EI-B (HITACHI M-80B) , Positive	splash10-03di-9000000000-90144d1440b06340fe7e	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negative	splash10-0udi-0900000000-99bad9fba8cf3bc081e3	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negative	splash10-0udi-0900000000-95b1b8722cad92c490e7	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negative	splash10-0udi-2900000000-d6ebac4ebed40b98b291	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negative	splash10-0udi-9000000000-94459eb26bcb7c315bcd	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negative	splash10-0a4i-9000000000-e212c5cbe08c4eb40b95	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-0udi-0900000000-99bad9fba8cf3bc081e3	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-0udi-0900000000-95b1b8722cad92c490e7	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-0udi-2900000000-d6ebac4ebed40b98b291	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-0udi-9000000000-94459eb26bcb7c315bcd	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-0a4i-9000000000-e212c5cbe08c4eb40b95	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-IT , negative	splash10-0udi-3900000000-dd2e8ada707700a86c15	JSpectraViewer \| MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0udr-9700000000-3b6086e299b180404c66	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0a4u-9100000000-1c4280d0a9143e3d48d0	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-052f-9000000000-bc80b097ba0f51c3ca40	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0udi-2900000000-a4de42a48fe44ac339fa	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0zfr-9800000000-543e60b2b278c1d51c48	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a4l-9000000000-6b15e313e3ee4ada68aa	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-001i-9100000000-e626913b2548db6c8608	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-001i-9000000000-a5c7e6b5fe910559a628	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-014i-9000000000-890b839f8e2f9ac3fd83	JSpectraViewer
MS	Mass Spectrum (Electron Ionization)	splash10-03di-9000000000-9246123374d3104316a3	JSpectraViewer \| MoNA
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
2D NMR	[1H,13C] 2D NMR Spectrum	Not Available	JSpectraViewer

References

References:

Yannai S. Dictionary of food compounds with CD-ROM: additives, flavors, and ingredients. Chapman & Hall/CRC; 2004.

Synthesis Reference:

Ruiz, Maria Olga; Cabezas, Jose Luis; Escudero, Isabel; Coca, Jose. Valeric acid extraction with tri-n-butyl phosphate impregnated in a macroporous resin: II. Studies in fixed bed columns. Journal of Chemical Technology and Biotechnology (2006), 81(

External Links:

Resource	Link
CHEBI ID	17418
HMDB ID	HMDB00892
Pubchem Compound ID	7991
Kegg ID	C00803
ChemSpider ID	7701
FOODB ID	FDB003230
Wikipedia	Valeric_acid
BioCyc ID	Not Available

Structure for #<Compound:0xacfc8918>